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Results
DOPAL
Characterization after reaction
TLC of 3:1 methylenechloride methanol
with iodine to stain.
HMR(with integration)
.
HMR extension
.
NMR 8.5-9.7
solubility: good in methanol, poor in methylene chloride
HMR(w/o integration) D2O added
making 16B (note: the scale is way off)
Ugi Reaction
Characterization of Starting Materials
Piperonal
(Used from same bottle in Exp076)
Aniline
Boc-Gly-OH
tertbutylisocyanide
Part I: Imine Formation
H NMR 1 hr 084A
H NMR 24 hrs 084B
H NMR 3 days 084C
PartII: Addition of Acid and Isocyanide
H NMR 2 hrs 084D
Overlays
ImineRxn overlay
UgiRxn overlay
Imine Reversal
Characterization of Starting Materials
Piperonal
Tert-butylamine
2-morpholinoethyl isocyanide
Boc-Gly-OH
Characterization of PartI: Imine Formation
48PtI_A t=04mins
48PtI_B t=12mins
48PtI_C t=19mins
48PtI_D t=25mins
48PtI_E t=50mins
48PtI_F t=56mins
48PtI_G t=94mins
Characterization of PartII - Addition of Boc-Gly-OH
48PtII_A t=04mins
48PtII_B t=14mins
48PtII_C t=20mins
Overlays
Overlay1
consists of HMRs piperonal, tertbutylamine, 12min,25min,50min,94mins from Part-I
Overlay2
consists of HMRs piperonal, tertbutylamine, Boc-Gly-OH, A-C from Part-II and G from Part-I
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Results
DOPAL
Characterization after reactionTLC of 3:1 methylenechloride methanol with iodine to stain.
HMR(with integration). HMR extension. NMR 8.5-9.7
solubility: good in methanol, poor in methylene chloride
HMR(w/o integration) D2O added making 16B (note: the scale is way off)
Ugi Reaction
Characterization of Starting MaterialsPiperonal(Used from same bottle in Exp076)
Aniline
Boc-Gly-OH
tertbutylisocyanide
Part I: Imine Formation
H NMR 1 hr 084A
H NMR 24 hrs 084B
H NMR 3 days 084C
PartII: Addition of Acid and Isocyanide
H NMR 2 hrs 084D
Overlays
ImineRxn overlay
UgiRxn overlay
Imine Reversal
Characterization of Starting MaterialsPiperonal
Tert-butylamine
2-morpholinoethyl isocyanide
Boc-Gly-OH
Characterization of PartI: Imine Formation
48PtI_A t=04mins
48PtI_B t=12mins
48PtI_C t=19mins
48PtI_D t=25mins
48PtI_E t=50mins
48PtI_F t=56mins
48PtI_G t=94mins
Characterization of PartII - Addition of Boc-Gly-OH
48PtII_A t=04mins
48PtII_B t=14mins
48PtII_C t=20mins
Overlays
Overlay1 consists of HMRs piperonal, tertbutylamine, 12min,25min,50min,94mins from Part-I
Overlay2 consists of HMRs piperonal, tertbutylamine, Boc-Gly-OH, A-C from Part-II and G from Part-I
Back to my page
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Discussion